NP-MRD: Showing NP-Card for 7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione (NP0326446)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 08:00:08 UTC

Updated at

2022-09-12 08:00:08 UTC

NP-MRD ID

NP0326446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione

Description

Vescalin, also known as castalagin or vescalene, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Vescalin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Vescalin has been detected, but not quantified in, nuts. 7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione is found in Castanea crenata, Castanea sativa, Melaleuca quinquenervia, Quercus petraea, Quercus salicina and Terminalia catappa. This could make vescalin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241211422D          

 45 50  0  0  0  0            999 V2000
    1.9427   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061   -2.4370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6388    0.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    1.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4796    1.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211    2.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    2.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482    3.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0061   -0.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    1.8239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0133    1.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592    0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -0.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248   -1.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3166   -2.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021   -3.0819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3376    0.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472    1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    2.3342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -0.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3723   -0.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305    0.7361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    3.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612    2.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209    2.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    2.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188   -1.7689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454   -2.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263   -2.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -3.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9214   -3.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7369   -3.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968    1.5788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4540    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9259    0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    0.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3182   -1.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -0.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8120   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650   -1.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678   -1.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -1.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 33  1  0  0  0  0
  1 44  2  0  0  0  0
  3  4  2  0  0  0  0
  3 23  1  0  0  0  0
  3 42  1  0  0  0  0
  4  5  1  0  0  0  0
  4 37  1  0  0  0  0
  5  6  1  0  0  0  0
  5 27  2  0  0  0  0
  6  7  2  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 26  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 29  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 35  2  0  0  0  0
 31 32  1  0  0  0  0
 31 43  2  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 41  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END

     RDKit          3D

 65 70  0  0  0  0  0  0  0  0999 V2000
   -2.7492    1.7937    1.9946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1458    1.2330    0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130    1.5079    0.5327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579    1.8215    0.7999 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7165    2.2519    2.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0580    3.3652    2.6367 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0450    2.7646   -0.2128 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2765    3.9277   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208    2.1082   -1.6127 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4374    0.8959   -1.4999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099   -0.0810   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2696   -0.0060   -2.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4126   -1.2031   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5937   -1.7378   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857   -2.9467    0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7244   -3.4773    1.1850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291   -3.7500    0.6635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502   -4.9597    1.3051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -3.2196    0.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432   -4.0808    0.1974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7544   -2.0447   -0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1374   -1.3518   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6992   -1.3528    0.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4013   -2.3781    1.6979 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5655   -0.3977    1.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327   -0.3761    2.4775 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8523    0.6060    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7118    1.6635    0.7235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085    0.6080   -0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4537   -0.3422   -1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605   -0.1639   -2.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652   -0.7903   -3.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389    1.0679   -3.3729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2638    2.1859   -2.3792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5751    1.9030   -1.6373 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6331    1.8002   -2.5040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791   -1.0092   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0871    0.2845    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4093    0.7829    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4611    0.0637   -0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7414    0.6533   -0.3747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282   -1.2078   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2318   -1.9768   -1.2449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9552   -1.7320   -0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7970   -3.0441   -1.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    0.8761    0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123    2.3684    2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287    1.3989    2.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    4.1007    2.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0327    3.0532    0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214    4.4515   -1.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3735    2.9127   -2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417   -2.9619    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -5.3626    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7304   -3.8990   -0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786   -2.3968    2.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0064   -1.0400    3.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1051    1.6593    1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    3.0726   -3.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962    2.7027   -0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1696    2.6368   -2.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607    1.8032    0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5436    0.2089   -0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1744   -1.6677   -1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390   -3.5760   -1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 38  1  0
 38 37  2  0
 37 44  1  0
 44 45  1  0
 44 42  2  0
 42 43  1  0
 42 40  1  0
 40 41  1  0
 40 39  2  0
 37 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9 34  1  0
 34 33  1  0
 33 31  1  0
 31 32  2  0
 31 30  1  0
 30 29  1  0
 29 35  1  0
 35 36  1  0
 29 27  2  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 23  2  0
 23 24  1  0
 23 22  1  0
  9  7  1  0
  7  8  1  0
  7  4  1  0
 39 38  1  0
 13 14  2  0
 35 34  1  0
 22 21  1  0
 22 30  2  0
  6 49  1  0
  5 47  1  0
  5 48  1  0
  4 46  1  6
 45 65  1  0
 43 64  1  0
 41 63  1  0
 39 62  1  0
 16 53  1  0
 18 54  1  0
 20 55  1  0
  9 52  1  6
 34 59  1  6
 35 60  1  1
 36 61  1  0
 28 58  1  0
 26 57  1  0
 24 56  1  0
  7 50  1  1
  8 51  1  0
M  END


  Mrv0541 02241211422D          

 45 50  0  0  0  0            999 V2000
    1.9427   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061   -2.4370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6388    0.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    1.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4796    1.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211    2.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    2.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482    3.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0061   -0.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    1.8239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0133    1.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592    0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -0.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248   -1.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3166   -2.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021   -3.0819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3376    0.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472    1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    2.3342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -0.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3723   -0.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305    0.7361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    3.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612    2.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209    2.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    2.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188   -1.7689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454   -2.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263   -2.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -3.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9214   -3.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7369   -3.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968    1.5788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4540    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9259    0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    0.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3182   -1.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -0.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8120   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650   -1.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678   -1.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -1.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 33  1  0  0  0  0
  1 44  2  0  0  0  0
  3  4  2  0  0  0  0
  3 23  1  0  0  0  0
  3 42  1  0  0  0  0
  4  5  1  0  0  0  0
  4 37  1  0  0  0  0
  5  6  1  0  0  0  0
  5 27  2  0  0  0  0
  6  7  2  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 26  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 29  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 35  2  0  0  0  0
 31 32  1  0  0  0  0
 31 43  2  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 41  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C3=C2C(=O)OC(C2OC(=O)C4=C(C2O)C(O)=C(O)C(O)=C34)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H20O18/c28-2-5-14(31)23-24-20(37)12-11(27(42)45-24)9(18(35)22(39)19(12)36)8-10(26(41)44-23)7(16(33)21(38)17(8)34)6-3(25(40)43-5)1-4(29)13(30)15(6)32/h1,5,14,20,23-24,28-39H,2H2

> <INCHI_KEY>
PPUHUWSVCUJGTD-UHFFFAOYSA-N

> <FORMULA>
C27H20O18

> <MOLECULAR_WEIGHT>
632.4369

> <EXACT_MASS>
632.064963836

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
54.83671683910817

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11(28),12,14,16(21),17,19-nonaene-4,22,27-trione

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
-0.41725373433333324

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.755850814770209

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2434615959886175

> <JCHEM_PKA_STRONGEST_BASIC>
-5.356890359953938

> <JCHEM_POLAR_SURFACE_AREA>
321.66

> <JCHEM_REFRACTIVITY>
142.07889999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
castalin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.626  -4.443   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.611  -4.549   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.832   0.056   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.192   1.554   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.512   3.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.895   3.276   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.279   4.011   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.730   5.401   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.517   6.674   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -5.611  -1.780   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -5.148   3.405   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.758   2.856   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.844   1.251   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.446  -0.284   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.090  -1.672   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.406  -3.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.324  -4.311   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.924  -5.753   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.497   1.654   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.328   3.065   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.486   4.357   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.956  -0.742   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.695  -0.144   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.804   1.374   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.343   7.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.114   5.507   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.972   4.503   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.417   4.995   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.902  -3.302   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.018  -4.483   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.609  -4.192   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.381  -5.653   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.800  -5.727   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.587  -7.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.376  -5.887   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.541   2.947   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.714   1.666   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.595   0.387   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.122   0.591   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       4.327  -1.926   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.049  -1.002   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.516  -1.303   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.241  -2.899   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.740  -3.262   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       5.334  -2.544   0.000  0.00  0.00           O+0
CONECT    1    2   33   44                                                  
CONECT    2    1                                                            
CONECT    3    4   23   42                                                  
CONECT    4    3    5   37                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8                                                            
CONECT   10   15                                                            
CONECT   11   12                                                            
CONECT   12    7   11   13                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   22                                                  
CONECT   15   10   14   16                                                  
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   13   20                                                       
CONECT   20    6   19   21                                                  
CONECT   21   20                                                            
CONECT   22   14   23                                                       
CONECT   23    3   22   24                                                  
CONECT   24   23                                                            
CONECT   25   26                                                            
CONECT   26    8   25   27                                                  
CONECT   27    5   26   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   43                                                  
CONECT   32   31   33                                                       
CONECT   33    1   32   34                                                  
CONECT   34   33                                                            
CONECT   35   30                                                            
CONECT   36   37                                                            
CONECT   37    4   36   38                                                  
CONECT   38   37   39   41                                                  
CONECT   39   38                                                            
CONECT   40   41                                                            
CONECT   41   38   40   42                                                  
CONECT   42    3   41   43                                                  
CONECT   43   31   42   44                                                  
CONECT   44    1   43   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
Vescalagin, (33beta)-isomer	HMDB
Castalagin	HMDB
Vescalagin	HMDB
Vescalene	HMDB
Vescalin	MeSH

Chemical Formula

C₂₇H₂₀O₁₈

Average Mass

632.4369 Da

Monoisotopic Mass

632.06496 Da

IUPAC Name

7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11(28),12,14,16(21),17,19-nonaene-4,22,27-trione

Traditional Name

castalin

CAS Registry Number

Not Available

SMILES

OCC1OC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C3=C2C(=O)OC(C2OC(=O)C4=C(C2O)C(O)=C(O)C(O)=C34)C1O

InChI Identifier

InChI=1S/C27H20O18/c28-2-5-14(31)23-24-20(37)12-11(27(42)45-24)9(18(35)22(39)19(12)36)8-10(26(41)44-23)7(16(33)21(38)17(8)34)6-3(25(40)43-5)1-4(29)13(30)15(6)32/h1,5,14,20,23-24,28-39H,2H2

InChI Key

PPUHUWSVCUJGTD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Castanea crenata	LOTUS Database	35616633
Castanea sativa	LOTUS Database	35616633
Melaleuca quinquenervia	LOTUS Database	35616633
Quercus petraea	LOTUS Database	35616633
Quercus salicina	LOTUS Database	35616633
Terminalia catappa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Gallic acid or derivatives
Benzopyran
Isochromane
2-benzopyran
Tricarboxylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.14	ALOGPS
logP	-0.42	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	7.24	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	321.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	142.08 m³·mol⁻¹	ChemAxon
Polarizability	54.84 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031746

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008415

KNApSAcK ID

Not Available

Chemspider ID

90329

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99973

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione (NP0326446)

MOL for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

3D MOL for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

3D SDF for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

3D-SDF for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

PDB for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

3D PDB for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

SMILES for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

INCHI for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

Structure for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)

3D Structure for NP0326446 (7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16(21),17,19-nonaene-4,22,27-trione)